This proposal is aimed at developing the basic organometallic chemistry necessary for utilizing transition metal-based reagents to form new carbon-oxygen (C-O) and carbon-nitrogen (C-N) bonds in organic molecules. Initial experiments outlined are designed to yield general methods for the preparation of metal-alkoxy, -hydroxy and amido complexes. It is then proposed to induce such species to undergo transformations (e.g., insertion, oxidative addition, reductive elimination) analogous to those known for metal alkyl complexes, and use these basic reactions to develop ways to transfer the electronegative ligands to organic and small-molecule substrates such as alkenes, alkynes and CO. Special attention is paid to the study of alkylideneamido complexes, which are capable of bearing chiral ligands and thus can be used to prepare optically active amines from achiral substrates. Plans are also outlined to prepare and examine the role of oxa- and azametallacycles in alkene oxidation processes, and to explore the possibility of developing new metal-based organic oxidation reagents by examining the reactions of low-valent metal complexes with controlled amounts of oxidizing agents such as O2, peroxides and peracids.